US4292218A - Low viscosity unsaturated polyester resins - Google Patents
Low viscosity unsaturated polyester resins Download PDFInfo
- Publication number
- US4292218A US4292218A US06/107,710 US10771079A US4292218A US 4292218 A US4292218 A US 4292218A US 10771079 A US10771079 A US 10771079A US 4292218 A US4292218 A US 4292218A
- Authority
- US
- United States
- Prior art keywords
- acid
- alkyd
- polyester resins
- styrene
- unsaturated polyester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D19/00—Producing buttons or semi-finished parts of buttons
- B29D19/04—Producing buttons or semi-finished parts of buttons by cutting, milling, turning, stamping, or perforating moulded parts; Surface treatment of buttons
Definitions
- the present invention relates to low viscosity unsaturated polyester resins, essentially comprising an unsaturated polyester alkyd and an ethylenically unsaturated monomer copolymerizable with the alkyd.
- the present invention relates also to the products, particularly buttons in all their marketable forms, obtained from said polyester resins by any processing technique suitable for such a purpose.
- unsaturated polyester resins obtained by mixing an unsaturated polyester alkyd with a copolymerizable monomer
- the known resins however have a higher viscosity, an inferior workability, a lower luster and an inferior resistance to repeated washings, than the resins of the present invention, the amount of monomer and the elastic modulus and heat distortion temperatures (HDT) of the hardened pure resin being equal.
- HDT elastic modulus and heat distortion temperatures
- An object of the present invention is low viscosity unsaturated polyester resins for making buttons, in all the marketable forms which can be made from polyester resins, by conventional processing techniques such as centrifugation and casting, essentially comprising
- alkyd having a molecular weight/double bond factor comprised between 300 and 390 and having an amount of free functional groups (constituted by hydroxyl groups+carboxyl groups) expressed as mg of KOH per g of alkyd, between 80 and 100 inclusive is employed as alkyd (A).
- the word "essentially” is to be construed, in the present specification, as meaning a content higher than 90% by weight.
- a preferably in molar amounts of 95% and 5% respectively
- adipic acid preferably in molar amounts of 95% and 5% respectively
- adipic acid preferably in molar amounts of 95% and 5% respectively
- adipic acid preferably in molar amounts of 95% and 5% respectively
- adipic acid preferably in molar amounts of 95% and 5% respectively
- adipic acid preferably in molar amounts of 95% and 5% respectively
- B styrene
- the turned buttons are easier to polish as a consequence of the milder action of the tools used for turning.
- the process for the preparation of the unsaturated polyester resins which are an object of the present invention does not differ from those generally known in the art, although attention must be paid to the fact that the amounts of reagents for producing the alkyd must be chosen in such a way as to obtain an alkyd which has a molecular weight/double bond factor comprised between 300 and 390 and an amount of free functional groups (constituted by hydroxyl groups+carboxyl groups) expressed as mg of KOH per g of alkyd, between 80 and 100 inclusive.
- the polyesterification reaction is carried out as usual at temperatures comprised between 150° and 250° C.
- buttons in all their marketable forms, obtained from the unsaturated polyester resins hereinbefore described, by the conventional unsaturated polyester resin processing techniques.
- Such techniques include, in particular, centrifugation and casting in bars or flat sheets, but others may be used.
- the peculiarity of the present invention consists in an improvement of the workability of the disc blanks and in the better physical and mechanical characteristics of the finished buttons as well as in the better ecological conditions which may be maintained in the workroom.
- the viscosity at 25° C. of the resin obtained is 1500 cps.
- the heat distortion temperature (HDT according to ASTM D648) of the hardened pure resin is 72° C.
- the gelling of the resin in the centrifuge occurs after 5 minutes. After 30 minutes the centrifuge is stopped and the soft sheet thus obtained is extracted.
- the sheet is laid on a plane.
- the sheet is punched with a conventional machine, whereby to obtain disc blanks which are further polymerized until a degree of hardness suitable for the following processing stages is obtained.
- buttons made from the aforesaid blanks by conventional processes, have the following improved characteristics, as compared to analogous buttons made from orthophthalic unsaturated polyester resins, usually employed for this purpose, prepared from propylene and/or diethylene glycols, maleic anhydride, phthalic anhydride and adipic acid:
- buttons are allowed to fall on a marble surface from a height of 10 m, the number of buttons which are chipped decreases by 30%;
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT31406/78A IT1160418B (it) | 1978-12-29 | 1978-12-29 | Resine poliestere insature a bassa viscosita' |
IT31406A/78 | 1978-12-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
US4292218A true US4292218A (en) | 1981-09-29 |
Family
ID=11233585
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/107,710 Expired - Lifetime US4292218A (en) | 1978-12-29 | 1979-12-27 | Low viscosity unsaturated polyester resins |
Country Status (9)
Country | Link |
---|---|
US (1) | US4292218A (fr) |
JP (1) | JPS55112224A (fr) |
CA (1) | CA1131831A (fr) |
DE (1) | DE2952678A1 (fr) |
FR (1) | FR2445358A1 (fr) |
GB (1) | GB2039508B (fr) |
GR (1) | GR74017B (fr) |
IT (1) | IT1160418B (fr) |
NO (1) | NO794339L (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4546142A (en) * | 1985-01-08 | 1985-10-08 | United States Steel Corporation | Inhibiting styrene emissions in unsaturated polyester resins |
US4663393A (en) * | 1984-10-12 | 1987-05-05 | Societe Chimique Des Charbonnages S.A. | Process for the manufacture of unsaturated polyester resins exhibiting linear maturing with magnesia |
CN105131194A (zh) * | 2015-09-30 | 2015-12-09 | 浙江伟星实业发展股份有限公司 | 一种人造牛骨纽扣及其制备方法 |
CN114262510A (zh) * | 2022-01-17 | 2022-04-01 | 浙江飞素服饰有限公司 | 一种环保谷物树脂纽扣及其制备方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1212746B (it) * | 1983-05-24 | 1989-11-30 | Snial Resine Poliestere Spa | Prodotti a base di poliesteri insaturi. |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2944994A (en) * | 1954-07-07 | 1960-07-12 | Robertson Co H H | Method of making transparent unsaturated polyester-styrene-glass fiber composition |
US2951823A (en) * | 1956-02-11 | 1960-09-06 | Ruetgerswerke Ag | Unsaturated polyesters of unsaturated alpha, beta-dicarboxylic acids and polyvalent alcohols |
US3511792A (en) * | 1966-07-09 | 1970-05-12 | Schering Ag | Unsaturated polyester resins formed between polymeric fatty alcohols and polycarboxylic acids |
US3715233A (en) * | 1970-09-18 | 1973-02-06 | Standard Oil Co | Process for preparing fiberglass preforms |
US3721642A (en) * | 1970-12-10 | 1973-03-20 | Diamond Shamrock Corp | Polymerizable unsaturated polyester composition containing thermoplastic additive |
US3736278A (en) * | 1970-12-23 | 1973-05-29 | Tokyo Shibaura Electric Co | Nil shrink unsaturated polyester resin composition |
US3830772A (en) * | 1971-05-19 | 1974-08-20 | Albert Ag Chem Werke | Thermo-setting moulding compositions and processes for their manufacture |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1769496A1 (de) * | 1967-06-02 | 1971-09-23 | Gen Tire & Rubber Co | Polyesterharz und seine Herstellung |
GB1276198A (en) * | 1968-10-23 | 1972-06-01 | Rohm & Haas | Moulding compositions |
GB1295371A (fr) * | 1969-12-23 | 1972-11-08 | ||
DE2258863A1 (de) * | 1971-12-10 | 1973-06-20 | Koppers Co Inc | Aushaertbare polyesterharzpraeparate |
DE2445958B2 (de) * | 1974-09-26 | 1978-10-12 | Hoechst Ag, 6000 Frankfurt | Knöpfe, Knopfplatten, Schnallen und Bijouterieartikel oder ihre Rohlinge, Verfahren und Formmasse zu ihrer Herstellung |
DE2509236A1 (de) * | 1975-03-04 | 1976-09-16 | Bayer Ag | Rieselfaehige, schwundarm haertbare formmassen auf basis ungesaettigter polyesterharze |
-
1978
- 1978-12-29 IT IT31406/78A patent/IT1160418B/it active
-
1979
- 1979-12-27 GR GR60857A patent/GR74017B/el unknown
- 1979-12-27 US US06/107,710 patent/US4292218A/en not_active Expired - Lifetime
- 1979-12-27 JP JP17389579A patent/JPS55112224A/ja active Pending
- 1979-12-28 DE DE19792952678 patent/DE2952678A1/de not_active Ceased
- 1979-12-28 FR FR7932051A patent/FR2445358A1/fr active Granted
- 1979-12-28 GB GB7944482A patent/GB2039508B/en not_active Expired
- 1979-12-28 NO NO794339A patent/NO794339L/no unknown
- 1979-12-28 CA CA342,793A patent/CA1131831A/fr not_active Expired
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2944994A (en) * | 1954-07-07 | 1960-07-12 | Robertson Co H H | Method of making transparent unsaturated polyester-styrene-glass fiber composition |
US2951823A (en) * | 1956-02-11 | 1960-09-06 | Ruetgerswerke Ag | Unsaturated polyesters of unsaturated alpha, beta-dicarboxylic acids and polyvalent alcohols |
US3511792A (en) * | 1966-07-09 | 1970-05-12 | Schering Ag | Unsaturated polyester resins formed between polymeric fatty alcohols and polycarboxylic acids |
US3715233A (en) * | 1970-09-18 | 1973-02-06 | Standard Oil Co | Process for preparing fiberglass preforms |
US3721642A (en) * | 1970-12-10 | 1973-03-20 | Diamond Shamrock Corp | Polymerizable unsaturated polyester composition containing thermoplastic additive |
US3736278A (en) * | 1970-12-23 | 1973-05-29 | Tokyo Shibaura Electric Co | Nil shrink unsaturated polyester resin composition |
US3830772A (en) * | 1971-05-19 | 1974-08-20 | Albert Ag Chem Werke | Thermo-setting moulding compositions and processes for their manufacture |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4663393A (en) * | 1984-10-12 | 1987-05-05 | Societe Chimique Des Charbonnages S.A. | Process for the manufacture of unsaturated polyester resins exhibiting linear maturing with magnesia |
US4546142A (en) * | 1985-01-08 | 1985-10-08 | United States Steel Corporation | Inhibiting styrene emissions in unsaturated polyester resins |
CN105131194A (zh) * | 2015-09-30 | 2015-12-09 | 浙江伟星实业发展股份有限公司 | 一种人造牛骨纽扣及其制备方法 |
CN105131194B (zh) * | 2015-09-30 | 2018-04-17 | 浙江伟星实业发展股份有限公司 | 一种人造牛骨纽扣及其制备方法 |
CN114262510A (zh) * | 2022-01-17 | 2022-04-01 | 浙江飞素服饰有限公司 | 一种环保谷物树脂纽扣及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
NO794339L (no) | 1980-07-01 |
GB2039508B (en) | 1983-03-02 |
FR2445358A1 (fr) | 1980-07-25 |
IT7831406A0 (it) | 1978-12-29 |
CA1131831A (fr) | 1982-09-14 |
IT1160418B (it) | 1987-03-11 |
FR2445358B1 (fr) | 1984-05-18 |
GR74017B (fr) | 1984-06-06 |
JPS55112224A (en) | 1980-08-29 |
DE2952678A1 (de) | 1980-07-10 |
GB2039508A (en) | 1980-08-13 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
AS | Assignment |
Owner name: SNIA VISCOSA SOCIETA' NAZIONALE INDUSTRIA APPLICAZ Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:CORRADO GIOVANNI;BERTOTTI ELVIO;SOPINO BRUNO;REEL/FRAME:003886/0239 Effective date: 19810716 |